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Cheap flights from New York to Chicago from $106

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/12. Fares are subject to change and may not be available on all flights or dates of travel.
NYC — CHI
6 Dec — 13 Dec1
1 adult
1 adult, Economy, 0 bags

Cheapflights Tip: The best prices from New York to Chicago are usually found in January or February, booked 64 days in advance, depart on a Tuesday or Monday and return on a Thursday

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Cheapest flights from New York to Chicago
Explore the most affordable flight options available from New York to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 6 November 2025.

Sat 6/1205:59EWR - ORD
1 stop6h 55mFrontier
Mon 8/1211:44ORD - EWR
1 stop8h 51mFrontier
Deal found 4/11$199
Sat 22/1111:05EWR - ORD
1 stop13h 01mSpirit Airlines
Mon 24/1114:01ORD - EWR
Nonstop2h 09mSpirit Airlines
Deal found 3/11$202
Thu 13/1115:22EWR - ORD
Nonstop2h 43mUnited Airlines
Wed 10/1206:00ORD - EWR
Nonstop2h 07mUnited Airlines
Deal found 5/11$203
Mon 1/1211:35EWR - ORD
Nonstop2h 21mSpirit Airlines
Wed 3/1214:01ORD - EWR
Nonstop2h 09mSpirit Airlines
Deal found 3/11$208
Wed 3/1207:00EWR - ORD
Nonstop2h 47mUnited Airlines
Mon 8/1215:35ORD - EWR
Nonstop2h 21mUnited Airlines
Deal found 5/11$211
Fri 5/1215:25EWR - ORD
Nonstop2h 44mUnited Airlines
Mon 8/1218:05ORD - EWR
Nonstop2h 23mUnited Airlines
Deal found 4/11$220
Mon 15/1221:57EWR - ORD
Nonstop2h 35mUnited Airlines
Thu 15/106:05ORD - EWR
Nonstop2h 10mUnited Airlines
Deal found 3/11$226
Thu 25/1207:59EWR - ORD
Nonstop2h 55mUnited Airlines
Thu 25/1215:53ORD - EWR
Nonstop2h 16mUnited Airlines
Deal found 4/11$228
Thu 13/1115:22EWR - ORD
Nonstop2h 43mUnited Airlines
Mon 17/1113:16ORD - EWR
Nonstop2h 13mUnited Airlines
Deal found 5/11$230
Tue 2/1218:59EWR - ORD
Nonstop2h 47mUnited Airlines
Thu 4/1221:08ORD - EWR
Nonstop2h 05mUnited Airlines
Deal found 3/11$231
Sat 13/1214:25EWR - ORD
Nonstop2h 39mUnited Airlines
Thu 18/1206:00ORD - EWR
Nonstop2h 10mUnited Airlines
Deal found 4/11$234
Thu 13/1108:00EWR - ORD
Nonstop2h 48mUnited Airlines
Tue 13/115:35ORD - EWR
Nonstop2h 16mUnited Airlines
Deal found 3/11$236

Cheap flight deals from New York to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from New York (NYC) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 6 November 2025.

Round-trip from

$199

One-way from

$106

Popular in

August

Cheapest in

January

Average price

$351

Good one-way deal

$136 or less
Frontier
  • Frontier
  • 6/12-8/12
  • 2 total stops
  • 15h 46m total
  • New York to Chicago
Search Deals
United Airlines
  • United Airlines
  • 4/12
  • Nonstop
  • 2h 42m total
  • New York to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($48 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average return price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a one-way flight from New York (NYC) to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customise your flight search to find flights from New York to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 647,157 searches. Data last updated 6 November 2025.
Use the filters below to find and compare flights from New York to Chicago that are best for you.

Fly from

New York

Fly to

Chicago

Route

Depart

Return

Price

NewarkChicago

EWR - ORD

EWRORD

Newark

Thu 11/12

07:00-08:47

Nonstop2h 47m

Chicago O'Hare Intl

Tue 16/12

11:51-14:59

Nonstop2h 08m

$211

NewarkChicago

EWR - ORD

EWRORD

Newark

Thu 4/12

14:25-16:04

Nonstop2h 39m

Chicago O'Hare Intl

Wed 10/12

06:00-09:07

Nonstop2h 07m

$211

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 5/12

15:25-17:09

Nonstop2h 44m

Chicago O'Hare Intl

Mon 8/12

18:05-21:28

Nonstop2h 23m

$220

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 27/1

21:22-22:59

Nonstop2h 37m

Chicago O'Hare Intl

Wed 28/1

09:02-12:18

Nonstop2h 16m

$242

NewarkChicago

EWR - ORD

EWRORD

Newark

Thu 15/1

06:00-09:40

1 stop4h 40m

Chicago O'Hare Intl

Sun 18/1

05:33-12:58

1 stop6h 25m

$273

NewarkChicago

EWR - ORD

EWRORD

Newark

Mon 24/11

06:00-10:19

1 stop5h 19m

Chicago O'Hare Intl

Wed 17/12

10:45-16:01

1 stop4h 16m

$288

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 19/12

08:00-09:55

Nonstop2h 55m

Chicago O'Hare Intl

Sun 28/12

19:59-23:15

Nonstop2h 16m

$288

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 8/4

07:00-08:30

Nonstop2h 30m

Chicago O'Hare Intl

Sun 12/4

06:00-09:06

Nonstop2h 06m

$288

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 16/12

07:05-12:10

1 stop6h 05m

Chicago O'Hare Intl

Sat 3/1

18:02-23:27

1 stop4h 25m

$296

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 10/3

13:00-18:46

1 stop6h 46m

Chicago O'Hare Intl

Wed 11/3

07:00-12:09

1 stop4h 09m

$317

Flights are sorted by cheapest return flights first.

Deals found on 5/11

Showing 1-10 of 22 results
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Best time to book a flight from New York to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from New York with our price prediction graph.
Estimated return price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from New York to Chicago

How far ahead should I book a flight from New York to Chicago?

Use this chart to determine the optimal time to book a return flight from New York to Chicago. Price data was last updated on 31 October 2025.

The best time to book flights from New York to Chicago is 64 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from New York to Chicago?

Currently, May is the cheapest month in which you can book a flight from New York to Chicago (average of $85). Flying from New York to Chicago in July is currently the most expensive (average of $194). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from NYC to CHI?

Find hourly flight availability from New York to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 6 November 2025.

When flying from New York to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 78% versus a flight at midday.

Weekly flight availability from New York to Chicago

Explore weekly flight availability from New York to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 6 November 2025.

The most flights from NYC to CHI are scheduled on a Monday (183 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (81 on average).

Related info for your journey

Find useful and relevant information for your journey from New York to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from New York to Chicago?

    Airlines like United Airlines and Delta fly from New York to Chicago in about 2h 47m. The time it takes to get you to your destination can typically vary by up to 1h 53m. New York and Chicago are separated by a distance of 1152 km. Both multi-stop and direct flights can be found to your destination and back.

  • What are the most reliable airlines from New York to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from New York to Chicago on time: Atlas Air (100%), Finnair (100%), Gulf Air (90%).

  • Can I find deals for flights from New York to Chicago that include hotel bookings?

    Yes. In addition to deals on New York to Chicago flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from New York to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from New York to Chicago.

  • Can I find deals for business class flights from New York to Chicago?

    Yes. Cheapflights offers flight deals from New York to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from New York to Chicago?

    Currently, May is the cheapest month in which you can book a flight from New York to Chicago (average of $85). Flying from New York to Chicago in July is currently the most expensive (average of $194). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for New York to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Newark to O'Hare Intl flights

Fly with Cheapflights

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How does Cheapflights help users find flights from New York to Chicago?

Cheapflights makes it easy to find New York to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from New York to Chicago?

Cheapflights helps you find that perfect flight to Chicago from New York by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from New York to Chicago with no change fees?

Yes, we can. To see specific flights from New York to Chicago with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from New York to Chicago become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Chicago from New York today and book when prices fit your budget.

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